At the end of that first night we spent together, she sent a picture of her cum-covered ass to her best friend/roommate/my sister. Obviously I was mortified, but at that point it was too late.
My sister, though, was pissed off, as expected. Within minutes she was blowing up my phone, calling me all sorts of names and using all kinds of colorful language. But after a couple days of sulking, she got over it. It wasn’t as big of a deal as Kelsey and I had expected. We had our night of fun and that was the end of it, we thought.
A month went by and nothing super notable went on between us. Kelsey started seeing somebody and I had a hookup with a girl I worked with a long time ago. I truly believed what happened between me and Kelsey that night was a one-time thing.
Then I got a text from Kelsey: “Hey, come over here and fuck me.”
I responded, “can’t your boyfriend do that?”
The little “typing” ellipse bubble appeared and disappeared a few times as she started and stopped her reply.
Eventually: “We broke up.”
Jackpot. Like I said, I figured it had been a one-time thing, but I’d secretly been hoping I’d get another round with her.
I was about to sit down to eat, so I texted her back and let her know it would be about an hour.
“But I don’t want to wait an hour,” she replied.
Another reply, in quick succession: “I want your cock inside me, daddy.”
Then she sent that damn picture of my cum on her back. “Remember how much fun we had last time?”
Of course I remembered.
“I’m on my way,” I said. Then, I followed up with: “Be ready for me.”
Her response: “Yes, daddy.”
I changed into some jeans and lost my boxer briefs (what was the use?) and got in my car. On the drive, I thought about the ramifications of what we were about to do. It wasn’t going to just be a one-time fling anymore. But that was good, right? After all, she’s sexy, I’m perpetually horny—that’s a pretty good arrangement.
I arrived at her place about 10 minutes later and headed up the steps before knocking on the door. A brief moment of panic as I scanned the parking lot for my sister’s car, but luckily, she was out doing something else that evening.
A few seconds later, Kelsey opened the door and ushered me inside.
She was wearing a robe that covered her shoulders down to her butt, but I assumed that wouldn’t be staying on for very long. I saw a hint of bare ass underneath, so she was clearly either naked or wearing a thong that covered the minimum area required to qualify as underwear. She grabbed my arm and led me to her bedroom, a surprisingly neat and tidy space with a made-up bed and everything in its place.
Kelsey smiled at me, sank to her knees, and unbuttoned my jeans, then unzipped my zipper enough to reveal my already-bulging cock. She reached inside and pulled it out, letting my shaft and balls breathe (finally). She bit her lower lip that sexy way she did the time before, then went to work.
The next few minutes were incredible. Kelsey has a gift when it comes to giving blowjobs—she has a way of working a cock with her mouth, tongue, and hands that just feels nothing short of amazing. Over the next several months I eventually lost count of how many times she made me cum with her mouth alone (more on that another time).
After she finished sucking my dick, she got up on the bed and beckoned me to come forward. I took off my shirt and for the first time really stared at her.
She was ultra-sexy that evening, wearing her pink robe over a set of white lingerie: a push-up bra decorated with lacy frills, with a matching thong that, as expected, covered very little of her pussy. On top of her smooth, tan skin, it looked fucking amazing.
I grabbed her around the waist and started kissing her, letting her robe fall to the bed as we moved up toward the headboard. My hands danced over her lower back and butt.
Kelsey was moaning almost uncontrollably already, which I thought was odd considering she hadn’t even really gotten naked yet.
Speaking of getting naked, I took the opportunity to slip out of my jeans. Our bodies pressed together and her hands wrapped around my shoulders as I got on top of her, my bare cock dragging slightly across her upper leg and over the side of her thong.
“Yes, daddy, drag that cock over my body.”
Despite the undeniable and overwhelming sex appeal oozing from her lingerie, I was more interested in what was underneath. That push-up bra made her tiny tits look incredible, but I wanted to get my hands on them. I reached around Kelsey’s back and unhooked her bra. Her breasts stumbled out as the bra made its way to the floor on the side of the bed. She kept moaning throughout, every touch seemingly sending her to a new high.
I put Kelsey back on her back and moved my head level with her tits. She closed her eyes as I started sucking on her left breast while fondling the other. My lips moved over the tiny mound, my tongue resting occasionally on her perky little nipple. My free hand worked its way down to her thong, briefly rubbing her pussy from the outside. Before too long, her thong was pulled aside, my hand working her already-wet pussy. It was clear to me that she’d already been playing with herself before I arrived.
In fact, she’d really been playing with herself. I suspected there had been some lube and maybe even a dildo involved. There was no way she was this wet just based on what we’d done so far.
Kelsey moaned further as my middle finger penetrated her pussy, easily sliding inside her warm, dripping slit. She fucking lost it.
I wiggled my finger around inside her, making a sort of “come here” motion with it as I drug it along the inner wall of her pussy. I matched the movement on the outside, using my other hand—now completely abandoning its place on her tits—to rub her mound. I noticed she had let a tiny little bit of hair grow back in the area just above her slit.
Then I noticed something a little lower—a glint of something pink caught my eye. I pulled on the sides of her thong, peeling it off her body and sliding it over her legs. Beneath Kelsey’s thong was a small pink jewel, the tip of a buttplug lodged inside her cute ass.
“Fuck, Kelsey,” I said. “Is that what I think it is?”
She bit her lower lip and nodded.
“No wonder you’re so turned on.”
She laughed a little and got up onto her knees, meeting me at my height and planting a big kiss on my lips. Her hands went low, her fist forming around my dick, tugging on it blindly.
For a few minutes we stayed like that, kissing each other inconsistently while she fondled my cock and balls.
Finally Kelsey gently turned me around and pushed me backward so that I was on the bed on my back. I repositioned myself so my legs weren’t dangling over the edge, then Kelsey climbed up on top of me.
Kelsey stretched her entire torso as she mounted me cowgirl-style. I guided my cock—now impossibly hard—into her pussy as she lowered herself onto me.
“Fuck, Kelsey, you’re so tight,” I commented. That buttplug must have been doing quite a number on her. I stayed still for a few moments while Kelsey adjusted to having my cock inside her. She rocked her hips back and forth, simultaneously rubbing her pussy against me and letting my cock slide in and out of her. Her tits looked amazing from this angle. Her nipples—rock hard at this point—are undoubtedly one of her best features, two perky little mounds atop her small breasts.